We shadow two It Girls in the making—Sky Ferreira and Rita Ora—who star in the resurrected ck one's first campaign

When Calvin Klein launched its gender-bending fragrance, ck one, in 1994, the ad campaign seared black-and-white images of Kate Moss, Stella Tennant, Kirsten Owen, and Jenny Shimizu slouching, posing, dancing, and making out into our premillennial psyche. Aggressive and relentlessly cool, the brand's ads were as game-changing (and controversial) as Brooke Shields' cheeky 1980 incantation about just what came between her and her Calvins.

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Fast-forward to 2011 and Calvin Klein is expanding ck one into a full lifestyle brand, including underwear, slouchy knits, and roughed-up jeans under the umbrella of the Calvin Klein brand. For a fresh campaign of risqué imagery that debuts this spring, the company has reunited the original team—photographer Steven Meisel and creative director Fabien Baron—to package the evolving brand's youthful spirit. They've cast more than 30 musicians (including budding pop stars Sky Ferreira and Rita Ora), models, and a variety of dilettantes—faces Baron describes as "young, cool, interesting, and charming for what they represent to people." According to Baron, "Ck one has always been about connecting with youth in a true and relevant way—its innocence, its authority, its arrogance, its sense of fun."

In the new surveillance-style commercials, billboards, and print ads, beautiful young people shift about in a white room, posing, gyrating, jumping, fighting, and breaking the fourth wall by leering and, at times, sneering at the camera—a clear effort to communicate the brand to the iPod generation, whose members were in OshKosh B'gosh during the heroin-chic era. "The '90s were more politically aggressive and a little bit more angry," says Kevin Carrigan, creative director for Calvin Klein and Calvin Klein Jeans. "There's an optimism in these kids and their lyrics."

ELLE shadowed two of Calvin's newest stars over two days on two continents for a glimpse of what life is like for It Girls in the making.

Sky Takes Manhattan

Browsing the racks at Manhattan vintage store Southpaw, 18-year-old singer Sky Ferreira says that her style was bicoastal even before she moved to New York City from her native Los Angeles last year. Ferreira, dressed in a leather biker jacket and tailored, knee-length navy dress, is well studied in incorporating '90s grunge and modern femininity, often pairing ankle combat boots and distressed T-shirts with girly blouses and floral dresses. And to think she was only two years old when the bewitchingly disheveled Kate Moss first invaded ck billboards.

While her personal style could suggest an angsty, soulful sound, Ferreira's As If!, which debuted in March, is upbeat and contagious, with digital enhancement that places her closer to Katy Perry than Courtney Love. (Two songs were produced by Bloodshy & Avant, the Swedish duo responsible for Britney Spears' Toxic, whom Ferreira contacted through...her MySpace page!) "It's not trying to be not poppy, and that's the point," Ferreira says of her sound. "I wanted to do straight pop. It's not ironic at all."

Stopping in Abracadabra, a costume store in Chelsea, Ferreira reaches up to retrieve a furry fox costume head, revealing one of her six tattoos, a teardrop hidden on the side of her finger. "I got this one because of Lil' Wayne," she explains. "But I'm kind of faking it, since I didn't actually kill anyone."

Ferreira persuaded her parents to let her move to New York shortly before her eighteenth birthday. Now she recites the typical complaints of someone who has left the order of the West Coast for the chaos of the East Village. "My first place was across the street from the bar Coyote Ugly, and people would ring my doorbell at three in the morning for no reason," Ferreira says. She has since moved to a doorman building nearby. "But other things here are easier. Like, I never learned how to drive." Around the corner from her new apartment, Ferreira halts on the sidewalk. "Ew!" she says. "Did you see that? That guy just rolled down his window and blew a kiss at me." And that never happened in L.A.?

"Who should we call to go to Beach Blanket Babylon?" asks 20-year-old singer Rita Ora as she applies the finishing touches–a few more soda-can-size curls, followed by a thick mist of hairspray–to her already buoyant platinum mane. Both her older sister, Elena, and BFF Kyle, a lanky stylist in a sheer black top and skinny pants, begin furiously typing away on their smartphones to round up the troops for a night out. "You really don't care about the ozone layer, do you?" Kyle mutters, motioning toward the rising plumes of hair product.

Ora, Jay-Z's latest protégé (she was signed to his Roc Nation label when she was 18), has just flown into London on a red-eye from L.A., where she's been polishing her forthcoming debut album of "English pop mixed with old-school hip-hop and soul." Slipping on a smattering of rings, spiked jewels, chains, and a tribalesque beaded pendant necklace to balance out the relative polish of her cream blazer and decidedly less demure black slipdress, the Kosovo-born, London-bred singer is clearly functioning on the far side of exhaustion. Still, making her way to the eternally cool Notting Hill restaurant known as BBB, she is exuberant, occasionally bursting into vocal runs—or, midsentence, a song lyric—in her honeyed, slightly husky voice.

"We used to go here for melon martinis when one of us got paid," says Ora, who, when not in New York, still lives with her parents and two siblings in subsidized housing near Portobello Road in West London. Her crew of old pals arrives—family friends, performing-arts-school classmates, and former coworkers from a sneaker shop—and they're a sartorially diverse bunch: a blur of red lips, statement hair, animal-print coats, leather jackets, and brash gold jewelry. After the hugs and screams subside, they order one round of dégradé lychee drinks, then follow it with another. Camera phones come out. The dancing begins.

And it continues, basically without pause, throughout a car ride and onto the group's next stop, the Queens Arms in Kilburn, an unassuming pub presided over—as luck would have it—by Ora's beaming father, Besnik. ("When I had no money," Ora says, "I'd come here all the time.") In this less glittery setting, as Ora sits surrounded by old friends and family, with traditional Albanian circle dancing carrying on in the back, it becomes clear how the singer's life is about to change, if all goes according to plan. She's hoping to hit the radio this summer with her first single, either a track written by the Ting Tings or one produced by will.i.am. And then there's a ck one–sponsored tour and her album release, tentatively scheduled for the fall. All of which means the pressure's on, but what of it? "I want it all to happen at once. I think it will be very powerful," Ora says.